Family-friendly holiday rentals in Callicoon

Cozy A-Frame | Hot Tub, Fire Pit & Pet-Friendly

Escape to the Cedar Haven A-Frame in Damascus, PA – the perfect romantic hideaway just a short drive from NYC. Nestled in peaceful woods, this cozy 400-square-foot retreat offers all you need for a relaxing escape. Soak in the private hot tub, roast marshmallows by the fire pit, or unwind to music as you watch the forest through wide windows. Whether celebrating a special occasion or just needing time away, the tiny cabin invites you to unplug, reconnect, and make memories in nature’s embrace.

The Schoolhouse at Kenoza Lake

The Schoolhouse at Kenoza Lake. This late 1800's renovated schoolhouse is the perfect getaway. Only a 2 hour drive from NYC. Old world charm with modern finishes. House features one bedroom plus a sleeping loft, a total of 3 beds plus a bunk bed, claw foot tub, cast iron wood stove, dinner barn, sleeping loft, vegetable garden, outdoor fire pit with bistro lights and Adirondack chairs. 10-20 min driving distance to all of Sullivan County's culinary offerings. 7 min drive to grocery store.

Chic Cabin on Callicoon Creek

***FEATURED IN ARCHITECTURAL DIGEST, TRAVEL & LEISURE, APARTMENT THERAPY, AND FODORS TRAVEL*** Set back on a small private road, this cabin dating back to the 1800s is perched above the Callicoon Creek, popular with fly fishermen casting for rainbow trout. Head up the wooded driveway and find yourself in a serene, green clearing all your own. The cabin and studio make for a peaceful getaway, shielded from the surroundings, but incredibly convenient for reaching nearby towns and activities.

Swimming Hole, OMG Game Barn! Hot Tub

Swimming hole in Callicoon Creek! 3,500 sq ft OMG Barn with 3 floors of fun: games, lounge, playground, billiards...! Stunning water views year-round. Excellent trout fishing. Two creeks merge together on the property. Cross the side creek into a forest oasis with 7 acres of nature trails. Callicoon has shops, restaurants and Delaware River access. FAST WiFi, Hot Tub, Firepit, Gas grill, Deck. 5 min to Seminary Hill. Villa Roma 9 minutes (skiing, tubing). We're renovated, clean and stocked.

3BR/2BA • Private Pool & Hot Tub Near Bethel Woods

A modern 3BR/2BA Catskills retreat with a private pool, hot-tub and fireplace. 10 mins away from Narrowsburg's shops and restaurants as well as Delaware River access for swimming and hiking. 15 mins to Bethel Concerts. Perched on a hill, offering scenic views and serenity- a true getaway destination. Enjoy modern decor, premium bedding, AC, fast Wi-Fi, and purest water that you’ll find. Swim, grill, play ping-pong, darts, star gaze. Pool season ends 9/14th. Hot tub is always open.

Chez Cochecton, a modern cabin in the Catskills

Completely renovated inside and out. This unique cabin style home is built for style and comfort. You'll love the thoughtful design and finishing touches. Enjoy some music and wine while relaxing in the private backyard. Cochecton and neighboring towns of Callicoon and Narrowsburg are full of amazing restaurants, shops and hangouts. Situated just off the Delaware River, this home is very close to swimming, hiking, and kayaking. Enjoy all the beautiful Catskills have to offer all year long!

Woodsy Retreat, Sunny Home with Paths and Stream

This lovely hand-made home in the woods, lined with windows, flooded with light, has 2 bedrooms and 2 full baths, and a large wraparound deck facing a feisty stream. It has 10 hilly acres of woods with its own paths to wander. Work, relax and play in its inspiring kitchen and lofty spaces stocked with albums, movies, books, art supplies, and instruments. Enveloped in nature, yet only a 10 minute drive to local hot spots including Narrowsburg, Callicoon, Skinners' Falls and Bethel Woods.

Cutest Little House in Narrowsburg

Relax in an idyllic wooded setting with 1000 feet of totally private river frontage, yet a 5 minute drive to Narrowsburg's restaurants and shops. If you like nature, privacy, history, vintage decor & design, this quaint 1950s cottage is for you. Hiking & campfires • Clawfoot tub • Front & back porches • Hummingbird & bunny watching • Den & WiFi • Peace & quiet • All included in your stay! Hundreds of 5-star reviews say it all. IG: #luxtonlake #tenmileriver #cutesthousenarrowsburg

Gorgeous Waterfront w/ Hot Tub and Game Level

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to Jay’s Big Sky! Here are a few things I think you’ll especially enjoy about the house. Highlights - You’ll love the: • Location - quiet, waterfront position on 27 acre lake • Hot tub (all year) - a relaxing treat after hiking, skiing, or exploring • Family-perfect layout - 2 levels, with full game / media level • Fast WiFi & dedicated workspace - ideal for remote work • Kayaks and life-vests - for safe water fun!

Delaware River retreat

Approximately two hours from the GW bridge - this beautiful country home is located directly on the Delaware River. The house features a full kitchen, a large dining room, and two porches that overlook the river. Watch the eagles, warm up by the fireplace, ski, hike, fish, canoe, swim, eat and laze about. With hi-speed cable and WiFi, tons of space inside and out, this house is perfect for a getaway, staycation, or for families and couples looking to remote-work.

Catskills Mountain Chalet l 5 Star experience !

Stylish Chalet in the world famous Catskill mountains privately tucked away on 12 acres surrounded by wildlife and nature. Year-round outdoor activities, fine dining, breweries, and boutique shopping all nearby. Enjoy it all here at Clover Fields! Why "Clover Fields" you ask? Deer visit our property almost daily to graze on our sweet clover fields. It's not uncommon to see them throughout the day. Other notable guests: fox, various birds, woodchucks, chipmunks.

Private Riverfront Catskills Retreat w/ Hot Tub

Tucked away on a private stretch of riverfront in the western Catskills, this cabin was made for unforgettable summer days. Morning coffee on the deck, afternoons by the river, golden-hour dinners outdoors, and fires under the stars. Inside, expansive picture windows, warm mid-century interiors, and thoughtful details create a space that's equal parts design-forward and deeply relaxing. Perfect for couples, families, friends, and dogs.